1. Field of the Invention
The present invention relates to a novel ruthenium metathesis catalyst and to a method for producing an olefin by using the ruthenium metathesis catalyst, and, more particularly, to a ruthenium metathesis catalyst used as a catalyst for a carbon-carbon bond formation reaction using various organic synthetic reactions, especially, a metathesis reaction and to a method for producing cyclic olefins, internal olefins or polyolefins.
2. Prior Art
Many transition metal complexes have been used as catalysts for organic synthetic reactions. Among these reactions, a metathesis reaction of an olefin by using a transition metal complex as the catalyst has been variously studied (R. H. Grubbs, W. Tumas, Science, 1989, 243, pp 907-915).
This reaction is conventionally used for synthesizing bioactive natural substances such as civetone, D.sup.9,12 -capnellane or 9-tricosene by using a tungsten type catalyst (WCl.sub.6 /EtAlCl.sub.2 or WCl.sub.6 /Cp.sub.2 TiMe.sub.2, wherein Et represents an ethyl group, Me a methyl group and Cp a cyclopentadienyl group) or a titanium type catalyst (Cp.sub.2 Ti(Cl)CH.sub.2 AlMe.sub.2) (Grubbs et al. Acc. Chem. Res. 1995, 28, pp446-452). The metathesis reaction is generally inferior in selectivity of type of reaction, yield, and stability to a variety of functional groups.
Recently, there has been a report that ring closing metathesis of nonconjugated diene and enone proceed using a molybdenum carbon complex catalyst in a highly selective and efficient manner (R. H. Grubbs et al. Acc. Chem. Res. 1995, 28, pp 446-452). This catalyst is, however, very unstable to many functional groups, oxygen and moisture.
For this, a ruthenium carbene complex which is relatively stable to air and moisture has been developed (WO 93/20111, WO 96/04289, WO 97/06185, F. Ozawa et al. 44th Symposium on Organometallic Chemistry, Japan. Abstracts, 1997, pp 74-75). This catalyst is effective for a ring closing metathesis reaction of nonconjugated dienes, ring opening metathesis polymerization of cyclic olefins, and the like. However, many steps are required to prepare this catalyst.
In order for the catalyst to be prepared in short steps, the catalyst is used in situ to carry out the ring opening metathesis polymerization of norbornene and cyclooctenes (A. F. Noels et al., J. Chem. Soc., Chem. Commun., 1995, pp 1127-1128; Macromolecules, 1997, 30, pp3127-3136). However, because these methods use unstable compounds (for example, diazo compounds), the production of a large amount of the catalyst is made with difficulty in actual industrialization. Hence the metathesis reaction using such a catalyst cannot be utilized on an industrial scale.